Gathering initially as part of a practical joke, members of "The Vicious Circle", as they dubbed themselves, met for lunch each day at the Algonquin Hotel from 1919 until roughly 1929.
At these luncheons they engaged in wisecracks, wordplay, and witticisms that, through the newspaper columns of Round Table members, were disseminated across the country.
In its ten years of association, the Round Table and a number of its members acquired national reputations, both for their contributions to literature and for their sparkling wit.
The group that would become the Round Table began meeting in June 1919 as the result of a practical joke carried out by theatrical press agent John Peter Toohey.
Woollcott's enjoyment of the joke and the success of the event prompted Toohey to suggest that the group in attendance meet at the Algonquin each day for lunch.
As they increased in number, Algonquin manager Frank Case moved them to the Rose Room and a round table.
Regulars at the game included Kaufman, Adams, Broun, Ross and Woollcott, with non-Round Tablers Herbert Bayard Swope, silk merchant Paul Hyde Bonner, baking heir Raoul Fleischmann, actor Harpo Marx, and writer Ring Lardner sometimes sitting in.
Harold Ross and Jane Grant once spent weeks playing a particularly memorable joke on Woollcott involving a prized portrait of himself.
They had several copies made, each slightly more askew than the last, and would periodically secretly swap them out and then later comment to Woollcott "What on earth is wrong with your portrait?"
No Sirree!, staged for one night only in April 30, 1922, was a take-off of a then-popular European touring revue called La Chauve-Souris, directed by Nikita Balieff.
Acts included: "Opening Chorus" featuring Woollcott, Toohey, Kaufman, Connelly, Adams and Benchley with violinist Jascha Heifetz providing offstage, off-key accompaniment; "He Who Gets Flapped", a musical number featuring the song "The Everlastin' Ingenue Blues" written by Dorothy Parker and performed by Robert Sherwood accompanied by "chorus girls" including Tallulah Bankhead, Helen Hayes, Ruth Gillmore, Lenore Ulric and Mary Brandon; "Zowie, or the Curse of an Akins Heart"; "The Greasy Hag, an O'Neill Play in One Act" with Kaufman, Connelly and Woollcott; and "Mr. Whim Passes By—An A.
the Round Tablers hoped to duplicate it with an "official" Vicious Circle production open to the public with material performed by professional actors.
Edna Ferber said she realized it when she arrived at the Rose Room for lunch one day in 1932 and found the group's table occupied by a family from Kansas.
H. L. Mencken, who was much admired by many in the Circle, was also a critic, commenting to fellow writer Anita Loos that "their ideals were those of a vaudeville actor, one who is extremely 'in the know' and inordinately trashy".
She sarcastically described a group she called "the Sophisticates": They met at the sign of the Indian Chief where the cleverest of them—and those who were so excitedly sure of their cleverness that for the moment they convinced others as well as themselves—foregathered daily.
There was a great deal of scintillating talk in this group of the significant books and tendencies of the day....They appraised, debated, rejected, finally placed the seal of their august approval upon a favored few.
[35] In 1996 the hotel was designated a national literary landmark by the Friends of Libraries USA based on the contributions of "The Round Table Wits".